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Chestertown Vacation Rentals

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Check prices for these dates

Tonight
Aug 14 - Aug 15
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Aug 15 - Aug 16
This weekend
Aug 15 - Aug 17
Next weekend
Aug 22 - Aug 24

Vacation Rentals in Chestertown

Lake George Escape - Campground
2 bedrooms, WiFi

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very Good, (164)
"Nice place to staying "
Lake George Escape - Campground
Waterfront Home on Lake George w/ Boat Dock!
House (2 Bedrooms) | Interior

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!
The Elms Waterfront Cottages
Condo | In-room dining

The Elms Waterfront Cottages

2.5 star property
8.4 out of 10, Very Good, (16)
"We were treated like royalty here at the Elms. The owner, Chandler and his staff, go above and beyond. What a beautiful escape. We will most definitely return. "
The price is ₩427,161
₩474,145 total
includes taxes & fees
Aug 24 - Aug 25
The Elms Waterfront Cottages
Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

Trout House Village Resort

3.0 star property
9.8 out of 10, Exceptional, (12)
"Absolutely wonderful place and super friendly staff "
The price is ₩197,367
₩253,554 total
includes taxes & fees
Sep 2 - Sep 3
Trout House Village Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"We had a great time. All the staff was helpful and courteous. The restaurant are nice and have good food. But if you want to change it up there is several restaurants in walking distance. We enjoyed Pete's dinner a small old timey cafe. The park across the road is also a nice place and occasionally has live music. The beds are hard if that's what you like. "
Lydia 4-night trip
Posted 1 day ago
The Queensbury Hotel

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

How many vacation rentals will I find in Chestertown?

With 62 Expedia vacation rentals, you're sure to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.

What’s a vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.